香豆素(Coumarin)是一类具有独特芳香气味的化合物,化学式为C9H6O2。它们属于苯骈α-呋喃酮类化合物,在自然界中广泛存在。
结构特征香豆素的基本结构由苯环和呋喃酮构成,其中苯环与四个碳原子相连的呋喃酮单元形成独特的“香豆素环”。
自然来源香豆素存在于多种植物、真菌及动物体内。在植物界中,它主要作为天然防御机制的一部分,用作对昆虫的化学信号。著名的例子包括:天竺葵科(如紫花苜蓿)、唇形科(如薄荷)和芸香科(如柑橘属果实)。此外,在真菌、苔藓及藻类中也有发现。
化学性质 稳定性由于其独特的结构,香豆素表现出良好的化学稳定性。它们不易被氧化或还原,但可以与其他化合物发生多种类型的反应,包括缩合、取代等。
生物活性许多香豆素衍生物具有生物活性,能够引起抗菌、抗炎、抗氧化等多种作用。这些特性使它们成为医药、食品添加剂等多个领域的重要研究对象。
应用领域 医药行业在制药业中,某些结构类似物被开发为药物先导化合物。例如,香豆素类抗生素是最早的广谱抗生素之一;一些香豆素衍生物还表现出抗癌潜力。
食品工业由于其独特的香气和味道,在食品加工中也得到了广泛应用,常作为香精成分使用。
其他应用此外,它们还在染料生产、农药开发等多个领域展现出潜在价值。
生产方法香豆素可通过多种合成路径获得。传统的化学合成涉及从苯甲醛出发的反应;而近年来,通过生物转化技术,利用微生物发酵过程制备天然香豆素也成为一种可持续的方法。
总之,香豆素因其独特的结构和广泛的生物学应用,在多个领域中发挥着重要作用,并且仍然是有机化学研究中的一个重要课题。
| 中文名称 | 英文名称 | CAS号 | 化学式 |
|---|---|---|---|
| —— | N'-tert-butyl-N-2,3-dihydro-2,4-dimethylbenzofuran-7-carbohydrazide | 1189819-03-1 | C15H22N2O2 |
| —— | 3-benzyl-2-methoxy-2,5-dimethyl-2,3-dihydro-benzofuran-3-ol | 63514-74-9 | C18H20O3 |
| —— | N-Butyl-7-tert-butyl-2,3-dihydro-3,3-dimethylbenzofuran-5-carboximidamide hydrochloride | 194600-71-0 | C19H30N2O*ClH |
| —— | 2.3-Dihydro-benzofuran-carbonsaeure-(2)-<2-hydroxy-aethylamid> | 114985-74-9 | C11H13NO3 |
| —— | N,N-dibenzyl-N-(2-allyl-7,8-dibenzyloxy-2H-chromen-4-ylmethyl)amine | 1313175-12-0 | C41H39NO3 |
| —— | N,N-dibenzyl-N-(2-adamant-1-yl-7,8-dibenzyloxy-2H-chromen-4-ylmethyl)amine | 1313175-21-1 | C48H49NO3 |
| —— | 2-(2,3-dihydro-1-benzofuran-5-yl)-5-[(2-methoxybenzyl)thio]-1,3,4-oxadiazole | 1005200-42-9 | C18H16N2O3S |
| —— | methyl (6-hydroxy-4,7-dimethyl-2,3-dihydro-1-benzofuran-3-yl)acetate | 1452479-74-1 | C13H16O4 |
| —— | 8-(2,4,6-trichlorophenyl)-N-cyclohexyl-1,2,3,4,4a,9b,-hexahydro[1]benzofuro[3,2-c]-pyridin-6-amine | 488124-47-6 | C23H25Cl3N2O |
| —— | methyl 6-chloro-c-3-hydroxy-3-methyl-2,3-dihydro-r-2-benzofurancarboxylate | 142143-65-5 | C11H11ClO4 |
| —— | 3-(2,3-dihydro-benzofuran-2-yl)-propan-1-ol | 84768-04-7 | C11H14O2 |
| —— | (+/-)-{[6-fluoro-7-(2-methylphenyl)-2,3-dihydro-1-benzofuran-2-yl]methyl}amine | 852282-17-8 | C16H16FNO |
| —— | 5-[4-(5-dodecylpyrimidine-2-yl)phenyl]-2-octylcoumaran | 160310-78-1 | C38H54N2O |
| —— | 10b-bromo-5a-hydrobenzofuro<2,3-b>benzofuran | 126536-06-9 | C14H9BrO2 |
| —— | 3<(acetylthio)methyl>-2,3-dihydrobenzofuran | 119286-03-2 | C11H12O2S |
| —— | tert-butyl 4-[6-(4-{[(2-hydroxyethyl)amino]carbonyl}phenyl)-4H-1,3-benzodioxin-2-yl]piperidine-1-carboxylate | 1200573-41-6 | C27H34N2O6 |
| —— | 3-[3-Hydroxy-4,6-dimethoxy-2-(4-methoxy-phenyl)-2,3-dihydro-benzofuran-2-yl]-propionitrile | 117828-37-2 | C20H21NO5 |
| —— | 1-((3R,4aS,9bS)-8,9b-Dimethyl-3,4,4a,9b-tetrahydro-dibenzofuran-3-yl)-piperidine | 68788-76-1 | C19H25NO |
| —— | 4b,9b-dihydrobenzo[b]benzofuro[2,3-d]furan | 7156-35-6 | C14H10O2 |
| —— | 8-(2,4,6-trichlorophenyl)-6-(methylthio)-1,2,3,4,4a,9b,-hexahydro[1]benzofuro[3,2-c]pyridine | 488125-19-5 | C18H16Cl3NOS |
| —— | N-[[5-(2,3-dihydro-1-benzofuran-5-yl)-1,3,4-oxadiazol-2-yl]methyl]-3-fluoroaniline | 1005200-95-2 | C17H14FN3O2 |
| —— | diethyl 3-hydroxy-7-methyl-1-benzofuran-2,2-(3H)-dicarboxylate | 1161815-26-4 | C15H18O6 |
| —— | trans-3,5-dichloro-2-fluoro-2,3-dihydrobenzofuran | 86324-85-8 | C8H5Cl2FO |
| —— | 2-(2-chloro-acetylamino)-8,9b-dimethyl-4a,9b-dihydro-4<i>H</i>-dibenzofuran-3-one | 61132-61-4 | C16H16ClNO3 |
| —— | [3-[(E)-2-(2,3-dihydro-benzofuran-5-yl)-vinyl]-6-(4-hydroxy-phenyl)-1H-pyrazolo[3,4-b]pyridin-4-yl]-piperazin-1-yl-methanone | 1426917-91-0 | C27H25N5O3 |
| —— | {(3S)-6-[(1R)-4-(1-methoxy-1,2,2-trimethyl-propyl)-indan-1-yloxy]-2,3-dihydro-benzofuran-3-yl}-acetic acid | 1380391-06-9 | C26H32O5 |
| —— | 2,8-dimethyl-2,5;8,11-diepoxido-benzo[1,2-<i>e</i>;4,5-<i>e'</i>]bis[1,2,4]trioxepin-5,11-dicarboxylic acid diethyl ester | 109846-27-7 | C18H18O12 |
| —— | [4-(2-methoxy-4-methyl-phenyl)-7-methyl-2-oxo-chroman-4-yl]-acetic acid | 109979-76-2 | C20H20O5 |
| —— | (9aS)-8-acetyl-1,7-dihydroxy-3-methoxy-9a-methyl-9-oxo-N-(2,3,5,6-tetramethyl-4-propoxybenzyl)-9,9a-dihydrodibenzo[b,d]furan-4-carboxamide | 925440-90-0 | C31H35NO8 |
| —— | 1-(5-Chloro-3,3-dimethyl-2,3-dihydro-benzofuran-7-yl)-4-[3-(2,6-dichloro-4-methanesulfonyl-phenoxy)-propyl]-piperazine | 349550-00-1 | C24H29Cl3N2O4S |
| —— | (1R,1aS,6aR)-1-(1a,6a-Dihydro-1H-6-oxa-cyclopropa[a]inden-1-yl)-methanol | 63730-26-7 | C10H10O2 |
| —— | 2-(5,7-Diiodo-4,6-dimethoxy-2,3-dihydro-benzofuran-3-yl)-ethanol | 119384-86-0 | C12H14I2O4 |
| —— | 3,3-dimethyl-2,3-dihydrobenzofuran-5-carboxylic acid | 75097-97-1 | C11H12O3 |
| —— | 6-methyl-3-phenylbenzofuran-2(3H)-one | 50341-19-0 | C15H12O2 |
| —— | [25,29,33,37-tetrakis(4-ethylphenyl)-12,18,39-tris(hydroxymethyl)-2,4,8,10,14,16,20,22-octaoxanonacyclo[21.15.1.124,38.05,36.07,34.011,32.013,30.017,28.019,26]tetraconta-1(39),5,7(34),11,13(30),17(28),18,23,26,31,35,38(40)-dodecaen-6-yl]methanol | 120476-29-1 | C68H64O12 |
| —— | 2,3-dihydro-7-iodo-2-methyl-5-trifluoromethoxybenzofuran | 467467-15-8 | C10H8F3IO2 |
| —— | (R)-5-methanesulfonyl-2-(2-piperidin-4-yl-2,3-dihydro-benzofuran-5-yl)-pyridine | 1382137-15-6 | C19H22N2O3S |
| —— | 8-(2,4,6-trichlorophenyl)-6-methyl-1,2,3,4,4a,9b,-hexahydro[1]benzofuro[3,2-c]-pyridine | 488124-95-4 | C18H16Cl3NO |
| —— | 8-(2,4-dichlorophenyl)-N,N-dipropyl-1,2,3,4,4a,9b,-hexahydro[1]benzofuro[3,2-c]-pyridin-6-amine | 488124-85-2 | C23H28Cl2N2O |
| —— | (-)-((2S,3S,4R)-2-methyl-4-(nitromethyl)chroman-3-yl)methanol | 1631165-85-9 | C12H15NO4 |
| —— | 2,3-Dihydro-4-tert-butyl-5-benzofuranol allyl ether | 119795-61-8 | C15H20O2 |
| —— | (1S)-1-(5-bromo-2,3-dihydro-1-benzofuran-7-yl)ethan-1-ol | 1568216-96-5 | C10H11BrO2 |
| —— | (2'R,4S,4a'R,9a'S)-2-amino-7'-(5-chloropyridin-3-yl)-1',2',3',4',4a',9a'-hexahydro-5H-spiro[oxazole-4,9'-xanthen]-2'-ol | 1379808-75-9 | C20H20ClN3O3 |
| —— | 2-methoxy-5-methyl-2-phenyl-2,3-dihydro-benzofuran-3-ol | 63514-78-3 | C16H16O3 |
| —— | (+/-)-6'-hydroxy-6-[3-(3-hydroxymethyl-5-methyl-1H-pyrazol-1-yl)propoxy]-4,4,4',4',7,7'-hexamethyl-2,2'-spirobichroman | 1078723-76-8 | C31H40N2O5 |
| —— | ethyl (2S)-2-methyl-2,3-dihydro-1-benzofuran-5-carboxylate | 1431865-03-0 | C12H14O3 |
| —— | (+/-) 2,2-Dimethyl-2,3-dihydro-benzofuran-7-carboxylic acid (4-oxo-2-pyrimidin-4-yl-4,6,7,8,9,10-hexahydro-pyrimido[1,2-a]azepin-10-yl)-amide | 1036716-75-2 | C24H25N5O3 |
| —— | trans-2,3-Dibrom-2,3,3a,8a-tetrahydrofuro<2,3-b>benzofuran | 72933-06-3 | C10H8Br2O2 |
| —— | 8-(2,4-dichlorophenyl)-N-ethyl-N-cyclohexyl-1,2,3,4,4a,9b,-hexahydro[1]benzofuro[3,2-c]pyridin-6-amine | 488124-84-1 | C25H30Cl2N2O |
| —— | 2-amino-7'-(5-chloropyridin-3-yl)-1',2',3',4',4a',9a'-hexahydro-5H-spiro[oxazole-4,9'-xanthen]-2'-ol | 1379811-15-0 | C20H20ClN3O3 |